Isolation, structure and iridium-mediated decarbonylation of a sodium fluorenone dianion complex

(Note: The full text of this document is currently only available in the PDF Version )

Zhaomin Hou, Yasuo Wakatsuki, Akira Fujita and Hiroshi Yamazaki


Abstract

Reaction of fluorenone with 2 equiv. of Na in THF at room temp. gave the polymeric Na–fluorenone dianion complex 1 in 79% isolated yield, which upon reaction with 0.5 equiv. of [(C5Me5)IrCl(µ-Cl)]2 afforded the decarbonylation product 2; both 1 and 2 have been structurally characterized.


References

  1. W. Schlenk and T. Weichel, Ber., 1911, 44, 1182 Search PubMed; H. Schlubach, Ber., 1915, 48, 12 Search PubMed; C. B. Wooster, J. Am. Chem. Soc., 1928, 50, 1388 CrossRef CAS; W. E. Bachmann, J. Am. Chem. Soc., 1933, 55, 1179 CrossRef CAS; P. J. Hamrick, Jr. and C. R. Hauser, J. Am. Chem. Soc., 1959, 81, 493 CrossRef; S. Selman and J. F. Easthan, J. Org. Chem., 1965, 30, 3804 CAS; E. L. Anderson and J. E. Casey, Jr., J. Org. Chem., 1965, 30, 3959 CAS; W. S. Murphy and D. J. Buckley, Tetrahedron Lett., 1969, 2975 CrossRef CAS; J. W. Huffman, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 8, ch. 1.4 Search PubMed; G. M. Robertson, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 3, ch. 2.6 Search PubMed.
  2. J. E. McMurry and L. R. Krepiski, J. Org. Chem., 1976, 41, 3929 CrossRef CAS; J. E. McMurry, M. P. Fleming, K. L. Kees and L. R. Krepiski, J. Org. Chem., 1978, 43, 3255 CrossRef CAS; J. M. Pons and M. Santelli, Tetrahedron Lett., 1982, 23, 4937 CrossRef CAS; J. E. McMurry, Acc. Chem. Res., 1983, 16, 405 CrossRef CAS; 1974, 7, 281; Chem. Rev., 1989, 89, 1513 Search PubMed; A. Fürstner and B. Bogdanovic, Angew. Chem., Int. Ed. Engl., 1996, 35, 2442 Search PubMed.
  3. Z. Hou, K. Takamine, Y. Fujiwara and H. Taniguchi, Chem. Lett., 1987, 2061 CAS; Z. Hou, K. Takamine, O. Aoki, H. Shiraishi, Y. Fujiwara and H. Taniguchi, J. Chem. Soc., Chem. Commun., 1988, 668 RSC; J. Org. Chem., 1988, 53, 6077 Search PubMed; H. Olivier, Y. Chauvin and L. Saussine, Tetrahedron, 1989, 45, 165 Search PubMed; Z. Hou, T. Yoshimura and Y. Wakatsuki, J. Am. Chem. Soc., 1994, 116, 11169 CrossRef CAS; T. Yoshimura, Z. Hou and Y. Wakatsuki, Organometallics, 1995, 14, 5382 CrossRef CAS.
  4. B. Bogdanovic, C. Kruger and B. Wermeckes, Angew. Chem., Int. Ed. Engl., 1980, 19, 817 CrossRef.
  5. Z. Hou, H. Yamazaki, K. Kobayashi, Y. Fujiwara and H. Taniguchi, J. Chem. Soc., Chem. Commun., 1992, 722 RSC; Z. Hou, H. Yamazaki, Y. Fujiwara and H. Taniguchi, Organometallics, 1992, 11, 2711 CrossRef CAS.
  6. J. E. Davies, J. Kopf and E. Weiss, Acta Crystallogr., Sect. B, 1982, 38, 2251 CrossRef.
  7. S. Brooker, F. T. Edelmann, T. Kottke, H. W. Roesky, G. M. Scheldrick, D. Stalke and K. H. Whitmire, J. Chem. Soc., Chem. Commun., 1991, 144 RSC.
  8. Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 2503 CrossRef CAS.
  9. S. Corbelin, J. Kopf and E. Weiss, Chem. Ber., 1991, 124, 2417 CAS.
  10. Q. Shen, M. Qi and Y. Lin, J. Organomet. Chem., 1990, 399, 247 CrossRef CAS.
  11. H. R. Luss and D. L. Smith, Acta Crystallogr., Sect. B, 1972, 28, 884 CrossRef CAS.
  12. Z. Hou, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1995, 117, 4421 CrossRef CAS; Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 7843 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.